


The Trails

by TheShyGirl



Category: Supernatural
Genre: Cruising, M/M, Outdoor Sex, Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2020-03-02
Updated: 2020-03-02
Packaged: 2021-02-28 07:33:43
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,200
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22979917
Author URL: https://archiveofourown.org/users/TheShyGirl/pseuds/TheShyGirl
Summary: Castiel Novak learns about a cruising locale in his new city. The eighteen-year-old wants to get some more experience under his belt (no pun intended) before going to college. So, he goes to check it out and ends up seeing something he didn't expect.*My work is only to be published on AO3. I do not give permission for this to be re-distributed through any app or other website.*
Relationships: Castiel/Dean Winchester
Comments: 6
Kudos: 129





	The Trails

**Author's Note:**

> I haven't written much in the past year, but I hope you find this one-shot enjoyable.

Castiel Novak jogged on, questioning his own sanity in coming here. Every now and then, moans and grunts from the nearby brush would reach his ears. Some though didn’t even bother to hide themselves from passersby. Men in various states of dress sucking and fucking for the world to see. 

That’s what this area of the woods was known for though. Men looking for like-minded fellows would come out to this secluded area to meet up for some fun of a sexual nature. Castiel had first heard about it from his brother who was joking about the area with his buddy. Having just moved to the new city at the beginning of the summer, he’d never known such a place existed.

“What’s The Trails?” Castiel had asked, made curious by the crude joke about it. 

“It’s where gay guys go for a fast fuck,” Gabriel informed him. “Don’t for a second think about going out there either. It’s nothing but old perverts. Not the kind of place for you.”

At first, Castiel had simply taken his word for it, but a couple months into his senior year of high school, he started getting antsy. There was only one other gay guy at his previous school and they had sex once. It was alright, but soon he’d be going off to college. He just wanted a little more experience. He knew there were a few more gay guys at his new school, but didn’t know exactly who they were and didn’t want to spend time figuring it out. He wasn’t looking for a relationship when he’d be leaving next summer anyway. 

So, late one Saturday afternoon, Castiel drove to the parking area at the edge of the woods. With his heart pounding, he took off jogging lightly down the trail. He really hadn’t known what to expect. In his mind, he kinda thought people would meet here and then go somewhere else. He realized how wrong he was when he caught sight of a man gripping a tree trunk while being plowed into from behind by a chubby guy off the path. He’d hurried past, but after that, there was no mistaking what the place was for. As he continued on, ignoring looks from men who were not preoccupied, he reconsidered whether or not he could do this. The only thing different from what he thought would be the location...and the fact that others could see them. Maybe, just once, it would be okay. _But how to find the right guy?_

Castiel was a little scared to slow down. It felt like if he stopped running, he might get pounced on. Forcing himself to slow, he began to walk until he saw a small dirt path to the left. Curious, he looked around and then turned down the path. He didn’t have to go far before hearing the grunts and praises of a man. A little further and they came into view, about fifteen feet to the right of the path. 

He had been very strict about keeping his eyes averted from those who were involved, but something about what he saw caught his eye. He stopped and watched. A man was leaning against a tree with his pants undone. On his knees in front of him, another man was presumably sucking his cock. It was hard to tell at the angle. What they were doing wasn’t what was of interest though. It was the jacket that the one on his knees was wearing. He’d seen it dozens of times since they’d moved. It was the green canvas that he’d come to associate with his handsome neighbor, Dean Winchester.

Dean lived next door with his younger brother, Sam, who was a junior in high school. The brothers were always nice when they saw them, waving, saying good morning, that kind of thing. They never really interacted and they certainly weren’t close enough to share details of their sexuality.

It really was too hard to tell for sure, but Castiel’s heart was thudding. The last thing he needed was his neighbor telling his parents where he saw him. He intended to walk on and ignore the possibility of Dean being gay, but his feet wouldn’t move. Then, he lost the chance. 

The man leaning against the tree looked up and saw Castiel staring at them. “Hey, kid! You wanna go at him? He sucks cock real good.”

The man on the ground half-turned, a smug grin on his face, to see who was watching. The grin melted and he jumped to his feet when he recognized his next-door neighbor. “Castiel…” 

Despite him whispering the name, Castiel felt it. As soon as Dean took a step in his direction, fight-or-flight kicked in and he ran.

“Shit!” Dean tore through the brush to get back to the path, chasing after him. “Cas! Cas, wait!”

Running at top speed through unfamiliar terrain was not Castiel’s forte. He didn’t know how far he’d made it, but his lungs were already burning when a hard body slammed into him, dragging him to the ground. With no fight in him, he found himself on his back with Dean straddling his hips and pinning his wrists to the ground. 

“Castiel, what the fuck? Why did you run?” In spite of huffing to catch his breath, he was still nearly shouting. 

Not knowing what else to do, Cas went right to begging. “Please don’t tell my parents I was out here! Please!”

Letting go, Dean sat up as he ran a hand through his hair. “Seriously?” he asked, looking down at the boy. “You think I would admit to my neighbors that I was out here? Even worse, ‘oh, by the way, I was at a local gay fuck spot with your underage son.’ Don’t think so.”

Castiel frowned. “I’m not underage. I’m eighteen.”

Dean rolled his eyes. “Well, that makes all the difference,” he muttered sarcastically. “I’m not going to say anything, but what are you doing here? You’re such a good kid. Do you know what could happen to you out here?”

With Dean making no move to get off him, Castiel gave a shrug as best as he could against the ground. “I was told guys meet up here. I just wanted some more experience before going to college next year. I don’t want to suck at sex.”

Chuckling, Dean said, “Even if you suck at sex, it’s still sex. You can ask any of the guys out here.” He nodded in the direction they came from. “It doesn’t have to be great; they just want to get off. It’s the same thing with the college crowd. They’re just younger.” After that, Dean went quiet, seemingly studying the pliant kid below him. Finally, he sighed and looked around. “If you want to go fuck one of these pervs, I won’t stop you, but I’m not going to let you be out here alone either. One of these sickos would knock you out and you’ll wake up tied up in someone’s basement.” He leaned down, placing his hands on either side of Castiel’s head, forcing him to meet his eyes. “Or you can fuck me.”

The shiver that ran through him had nothing to do with being on the cold ground. _He can’t be serious._ Things like this just don’t happen to Castiel. He’d made his peace with coming to the woods and getting it on with some stranger, but the possibility that it could be with Dean - Dean, his hot neighbor, who nearly gave him an aneurysm the first time Castiel saw him mowing without a shirt on. He couldn’t help being skeptical. “ _You_ ?! I would fuck _you_?”

“What? I’m a good guy and maybe I want to do it out of the goodness of my heart,” he said with a chuckle. After getting a skeptical frown, Dean sat back and looked back down the trail. “Well, I suppose we could get the guy I was sucking off. He’d definitely be interested in a pretty boy like you. If you don’t want him, there’s-”

Castiel gripped the edges of Dean’s coat and pulled causing Dean to have to put his hands down again to catch himself. “No. I want you.” The term ‘pretty boy’ was not something he’d ever taken as a compliment, but hearing Dean say it, it sounded different, like Dean actually found him attractive. 

The cocky smirk from earlier returned. “Really? Are you sure?”

He nodded. “Yeah.” The word had barely left his lips before Dean’s were pressed to them. The suddenness was a surprise, but Castiel was quick to catch up. He opened his mouth, inviting Dean’s tongue in, an invitation that was greedily accepted. 

Kissing wasn’t an activity Dean usually participated in while in the area, but something about Castiel, being so sweet, so naive, so innocent, just made him want a taste. It was absolutely exquisite. Castiel’s tongue was so soft and caressed his own gently. If he gave into kissing one of those old fucks out here, it usually meant a fat, slobbery tongue shoving into his mouth, trying to get down his throat. There was no doubt that Castiel was the much more enjoyable option. 

Castiel’s mind had short-circuited and he was running purely on instinct. His hands moved up under Dean’s jacket and shirt, feeling the warm skin beneath. He tried to touch as much as his position would allow. If he had been thinking clearly, he would have taken the time to try to memorize every sensation he was experiencing, including how Dean felt, but thinking was not something he was keen to do. It made it quite a shock when Dean pulled away to sit up, yet Castiel’s hands quickly resumed their exploration, tracing over his abs and up his sides. 

Dean shrugged off his coat, wishing that they were anywhere else. This place was nowhere for a boy like Castiel to be, but he wasn’t going to pass up the opportunity over location. With the jacket off, he grabbed Castiel’s wrists, pulling his hands from inside his Led Zeppelin t-shirt. He pressed a kiss to the knuckles and set them to each side. “Time for me to get my hands on you.” 

A little nod was all that Castiel could manage. He watched Dean scoot back onto his thighs, revealing the prominent tent in his shorts. As soon as he saw Dean reach for the waistband of his shorts, he let his head thunk back to the ground, sure he wouldn’t be able to handle the sight that would accompany the feeling. He felt his cock spring free of its confines and cool air rushed over it.

“Jesus! No eighteen year old should be packing that size.” He stroked up and down the length, excited by what he was seeing. Judging by Castiel’s suddenly sharp breaths, he was enjoying the attention. He smirked as he reached over for the discarded jacket, digging into the pocket. “It’s gonna be fun.” He pulled out a travel-size bottle of lube, a condom packet, and a handkerchief. Tossing the condom onto Castiel’s chest, he said, “Put this on.” While he watched Cas fumble with the condom, Dean worked on undoing his jeans, finally pulling out his own dick for some relief from the pressure. 

Castiel’s eyes went wide and he froze as he watched Dean pull on a cock that easily out-measured his own. 

Seeing the teen’s captivated expression, Dean chuckled. “What? Thinking you want to be the one getting fucked instead?”

While Cas had topped in his one sexual experience and had planned to do so in the woods, he’d played with his own ass enough to know he found it enjoyable, as well. He figured that made him a switch. As fun as he thought it would be, Dean was bigger than anything he’d previously used and he wasn’t even remotely prepared. “Kinda, but that’s way too big.”

“Thanks for the compliment,” Dean grinned. He moved from his spot on top of Castiel, settling on his knees next to him. “We don’t get naked out here. It’s just in case cops come through,” he explained as he scooted his jeans down to his knees. “So, we can stand up or you can fuck me like this.” He squeezed a bit of lube onto two of his fingers and reached behind himself. 

The squelching sound of Dean’s fingers going inside his ass made Castiel’s dick twitch in anticipation and he quickly returned to his task of opening the condom. “Th..th..this is-is fine,” he stammered as he flung the wrapper to the side. Rolling the condom on was a surprisingly quick task considering how long he’d taken to open the package. 

Castiel moved up onto his own knees, keeping his shorts in place. His first time had been a bumbling mess, but it was the first time for his partner, as well, so it was no big deal. The nerves over fucking someone as experienced as Dean were starting to set in. “Do you need more prep?” he asked hesitantly when Dean removed his fingers. 

“Nope. Any time I come out here, I get ready beforehand.” Dean used the handkerchief to wipe his hand and then handed the lube bottle to Castiel. “Just lube up and show me what you got.” Giving him a wink, Dean moved to all fours and looked over his shoulder, shaking his ass a bit.

The move made Cas smile and he poured some of the cool liquid into his hand. A few strokes had it well spread over his length. He scooted over behind Dean, finally taking a good hard look at the beauty of his ass. It was so well-rounded and there was a slight shine from the wetness that had been applied between his cheeks. 

Whatever nerves he’d been feeling disappeared. The sight of Dean’s waiting and eager ass was all he needed. He moved into place and with one hand guiding his dick, he slowly began to press in.

“Mmmm… Feels good.” Dean nearly purred the words. 

Encouraged, Cas pressed a little quicker, sinking fully in. The warmth and tight squeeze was perfection and he moaned over the delicious sensations. He really began to wonder why he hadn’t been having sex this whole time. There were so many missed opportunities for this incredible pleasure. Looking down at Dean, who was now on his forearms, Castiel couldn’t imagine anyone better to get started with. Perhaps he’d just been waiting for this moment. 

“You do know sex involves moving, right?” Dean snarked. The full feeling was great, but he came to the woods for a reason.

Thoughts of fate were quickly shaken from Castiel’s mind as he started to pull back and then thrust his hips forward. Hearing the grunt from Dean, he wondered if he could make him do it again. Repeating the move indeed got the same sound. Pleased, he picked up the pace. Focusing on Dean, rather than his own overwhelming pleasure, was allowing him to last longer than he expected. His fingertips dug into Dean’s hips as he pulled him back while thrusting forward. 

“Yeah! That’s it, Cas! Fuck, you’re good at this!”

Hearing those positive words was a fantastic incentive as he drove on even harder. His willingness to please was slowly being overcome by the waves of pleasure experienced with every thrust. His focus shifted from Dean’s sounds to moving in the way he liked the most. Getting off became top priority as he began to pump into Dean at a seemingly impossible pace. 

“Holy shit! Yes!” Dean was sure that getting fucked by Castiel was better than anything he might have experienced with the guy from before. The intensity was out of this world, making him feel like a drooling, inexperienced teen himself. Knowing that Castiel had to be getting close at this point, Dean balanced himself and managed to reach a hand underneath him to start stroking his own cock. 

Seeing what Dean was doing, Castiel felt better about completely letting go. His insides were tightening up and he was ready to blow. 

Dean beat him to it, groaning out a dozen curse words while his cum splattered on the dirt below. He felt his ass spasming, gripping Castiel in pulses and smiled when he heard the gasp.

That rippling feeling inside Dean was too much. That wire pulling tight within him snapped. He’d never heard such obscene noises and were even more surprised they were coming from him as he emptied himself into the condom. 

It took a few minutes of catching their breaths before Castiel finally felt he had the energy to pull back out of Dean. He grimaced at the mess of the condom and began to peel it off wondering what to do with it. 

“Here. Put it in here.” Dean had produced a small blue bag from his coat pocket. A small packet of wipes also appeared and he got to work, cleaning up his backside, before adding them to the bag. 

Once they were cleaned up with clothes righted and back on their feet, nerves came back to Castiel, leaving him feeling incredibly awkward. “So, um, thanks.”  
Dean huffed a laugh. “No need to thank me. That was incredible. I don’t know why you thought you needed more experience. You seem to know what you’re doing.”

Cas smiled at the comment, eyes on the ground. 

“Come on. I want to get you out of here before prying eyes come around.” Dean motioned for Castiel to follow and they headed back the way they’d come. 

The walk back was filled with silence between them, though the sounds of the forests and sexual adventures within gave them plenty to hear. Once they made it to the parking lot, Dean nodded towards his car. “Come ‘ere a minute.”

Castiel followed him over to the beautiful black beast of a vehicle that he’d seen so often in the driveway next to his home. He watched as Dean opened the passenger door and rummaged through the glove box, finally emerging with a pen and an old receipt.

Dean scrawled his number across the back of the receipt and held it out to Castiel. “Don’t ever come out here again. Next time you decide you want a little more ‘experience,’ call me instead. I’ll help.”

With a timid smile, Castiel accepted the paper, nodding. “Okay. Thank you, Dean.” He grimaced as Dean ruffled his hair before walking over to the driver's side of his Impala. 

“I’m not leaving this parking lot until I see you out of it, so you better get to your car.”

It wasn’t something he needed to be told twice. Despite the great time he’d just had with Dean, Castiel was desperate to get away from the depravity. He hurried off to his car, jumping in, and setting Dean’s number in his passenger seat. Unsurprisingly, the black Impala followed him most of the way, only veering from the path for a gas stop.

The whole way home, Castiel kept glancing at the number in the seat next to him. “I wonder when is too soon to call.”


End file.
